Extraction process for aldehyde product separation and catalyst recovery

An integrated process of hydroformylating a seed oil in its triglyceride form and extracting a hydroformylation product composition derived therefrom to separate an aldehyde product and to recover a hydroformylation catalyst, the process comprising:

• (a) hydroformylating a seed oil comprising a mixture of olefinically-unsaturated fatty acid triglyceride esters with carbon monoxide and hydrogen in the presence of a transition metal-organophosphine ligand complex catalyst wherein the organophosphine ligand is ionically-charged, optionally free ionically-charged organophosphine ligand, and a polar organic solubilizing agent for said complex and said optional free ligand, in a hydroformylation reactor under reaction conditions sufficient to obtain a non-aqueous hydroformylation product composition comprising a mixture of formyl-substituted fatty acid triglyceride esters, the transition metal-organophosphine ligand complex wherein the ligand is ionically-charged, optionally free ionically-charged organophosphine ligand, and the polar organic solubilizing agent for said complex and said optional free ligand;
• and thereafter
• (b) mixing the non-aqueous hydroformylation product composition with water and an extraction solvent having low water solubility under conditions sufficient to obtain by one or more stages of phase separation an organic phase comprising the mixture of formyl-substituted fatty acid triglyceride esters and the extraction solvent having low water solubility and an aqueous phase comprising the transition metal-organophosphine ligand complex wherein the ligand is ionically-charged, optionally the free ionically-charged organophosphine ligand, the polar organic solubilizing agent, and water.

An integrated process of hydroformylating a seed oil in its triglyceride form and extracting a hydroformylation product composition derived therefrom to separate an aldehyde product and to recover a hydroformylation catalyst, the process comprising:

• (a) hydroformylating a seed oil comprising a mixture of olefinically unsaturated fatty acid triglyceride esters and simultaneously hydroformylating a C3-6 olefin with carbon monoxide and hydrogen in the presence of a transition metal-organophosphine ligand complex catalyst wherein the organophosphine ligand is ionically-charged, optionally free ionically-charged organophosphine ligand, and a polar organic solubilizing agent for said complex and said optional free ligand, in a hydroformylation reactor under reaction conditions sufficient to obtain a non-aqueous hydroformylation product composition comprising a mixture of formyl-substituted fatty acid triglyceride esters, a C4-7 aldehyde capable of serving as an extraction solvent having low water solubility, the transition metal-organophosphine ligand complex wherein the ligand is ionically-charged, optionally free ionically-charged organophosphine ligand, and the polar organic solubilizing agent for said complex and said optional free ligand;
• and thereafter
• (b) mixing the non-aqueous hydroformylation product composition with water under conditions sufficient to obtain by one or more stages of phase separation an organic phase comprising the mixture of formyl-substituted fatty acid triglyceride esters and the C4-7 aldehyde serving as the extraction solvent having low water solubility and an aqueous phase comprising the transition metal-organophosphine ligand complex wherein the ligand is ionically-charged, optionally the free ionically-charged organophosphine ligand, the polar organic solubilizing agent, and water.